Palladium-Catalyzed C-P Coupling Reactions between Vinyl Triflates and Phosphine-Boranes: Efficient Access to Vinylphosphine-Boranes
Delphine Julienne; Jean-François Lohier; Olivier Delacroix; Annie-Claude Gaumont; Journal of Organic Chemistry 72 (2007) 2247–2250; doi:10.1021/jo062482o

data_4022805
_publ_contact_author_address
;     Laboratoire de Chimie Mol\'eculaire et Thio-organique, UMR CNRS 6507
      ENSICAEN - Universit\'e de Caen
      14050 Caen
      France
;
_publ_contact_author_email       annie-claude.gaumont@ensicaen.fr
_publ_contact_author_fax         '332 31 45 28 65'
_publ_contact_author_name        'Gaumont, Annie-Claude'
_publ_contact_author_phone       '332 31 45 28 73'
_publ_section_title
;
 Palladium-Catalyzed C-P Coupling Reactions between Vinyl Triflates
 and Phosphine-Boranes: Efficient Access to Vinylphosphine-Boranes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2247
_journal_page_last               2250
_journal_paper_doi               10.1021/jo062482o
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C18 H22 B P'
_chemical_formula_sum            'C18 H22 B P'
_chemical_formula_weight         280.14
_chemical_melting_point          368(2)
_chemical_name_systematic
;
 (cyclohex-1-en-1-yl)diphenyl phosphine borane
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.718(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3997(7)
_cell_length_b                   10.0174(8)
_cell_length_c                   17.1329(14)
_cell_measurement_reflns_used    7941
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.34
_cell_measurement_theta_min      2.97
_cell_volume                     1611.4(2)
_computing_cell_refinement       'APEX2 software'
_computing_data_collection       'APEX2 software'
_computing_data_reduction        'APEX2 software'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Nonius ApexII-CCD'
_diffrn_measurement_method       '\w scans and \f scan with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41977
_diffrn_reflns_theta_full        33.29
_diffrn_reflns_theta_max         33.29
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       quadratic
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method dichloromethane
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         12079
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0867P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                9071
_reflns_number_total             12079
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062482osi20061204_015313.cif
_cod_data_source_block           julienne1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022805