Insertion of benzyne into the Pd-C bond. Synthesis of unnatural amino acid derivatives by sequential insertion of benzyne and CO: 2,2'-functionalized biaryls containing alkylamino and carboxymethyl substituents. Isolation of stable carbopalladated-benzyne intermediates
Jose-Antonio Garcia-Lopez; Maria-Jose Oliva-Madrid; Isabel Saura-lamas; Delia Bautista; Jose Vicente; Chem.Commun. 48 (2012) 6744–; doi:10.1039/c2cc32975a

data_7107928
_publ_section_title
;
 Insertion of benzyne into the Pd-C bond. Synthesis of unnatural amino
 acid derivatives by sequential insertion of benzyne and CO:
 2,2'-functionalized biaryls containing alkylamino and carboxymethyl
 substituents. Isolation of stable carbopalladated-benzyne intermediates
;
_journal_name_full               Chem.Commun.
_journal_page_first              6744
_journal_paper_doi               10.1039/c2cc32975a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C35 H35 Br Cl2 N O2 P Pd'
_chemical_formula_weight         789.82
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.116(2)
_cell_angle_beta                 79.424(2)
_cell_angle_gamma                75.791(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8675(7)
_cell_length_b                   13.5117(11)
_cell_length_c                   15.0521(12)
_cell_measurement_reflns_used    5425
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.56
_cell_measurement_theta_min      2.56
_cell_volume                     1613.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       \w-scan
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19839
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    2.062
_exptl_absorpt_correction_T_max  0.9407
_exptl_absorpt_correction_T_min  0.8292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment
'NH2 free with SADI, rigid methyls others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7568
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+1.8269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                7000
_reflns_number_total             7568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc32975a.txt
_cod_data_source_block           joe6912s
_cod_database_code               7107928