Facile Regio- and Stereoselective Hydrometalation of Alkynes with a Combination of Carboxylic Acids and Group 10 Transition Metal Complexes: Selective Hydrogenation of Alkynes with Formic Acid
Ruwei Shen; Tieqiao Chen; Yalei Zhao; Renhua Qiu; Yongbo Zhou; Shuangfeng Yin; Xiangbo Wang; Midori Goto; Li-Biao Han; Journal of the American Chemical Society 133 (2011) 17037–17044; doi:10.1021/ja2069246

data_4106997
_publ_section_title
;
 Facile Regio- and Stereoselective Hydrometalation of Alkynes with a
 Combination of Carboxylic Acids and Group 10 Transition Metal Complexes:
 Selective Hydrogenation of Alkynes with Formic Acid
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17037
_journal_page_last               17044
_journal_paper_doi               10.1021/ja2069246
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C22 H40 O2 P2 Pd'
_chemical_formula_sum            'C22 H40 O2 P2 Pd'
_chemical_formula_weight         504.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.9390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.9093(10)
_cell_length_b                   18.9722(12)
_cell_length_c                   16.9307(11)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.32
_cell_volume                     4913.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            53857
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.33
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_correction_T_min  0.8064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.271
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         10708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+3.5328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                8310
_reflns_number_total             10708
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2069246_si_002_2.cif
_cod_data_source_block           2b
_cod_database_code               4106997